


orgasms and cold pizza

by naturegirl



Series: snapshots [1]
Category: Supernatural
Genre: F/M, Loss of Virginity, Lots of drinking, Smut, Soft Dean, virgin!reader
Language: English
Status: Completed
Published: 2020-05-01
Updated: 2020-05-01
Packaged: 2021-03-01 18:16:02
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,957
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23941426
Author URL: https://archiveofourown.org/users/naturegirl/pseuds/naturegirl
Summary: reader met dean senior year of hs Bc she looked out for Sam. She kept in touch with both of them (but more Sam). When Sam goes off to college a sad dean shows up on her doorstep with no warning.
Relationships: Dean Winchester/You
Series: snapshots [1]
Series URL: https://archiveofourown.org/series/1725841
Kudos: 33





	orgasms and cold pizza

**Author's Note:**

> this is the first part of a new series but they should be able to all be read on their own.

It may have been two am but I had yet to put down my book, so I was awake when I heard knocking at my front door. I wasn’t going to open it-because hello it was two am- but the knocking kept going so I was just going to tell them off. I opened the door to see a familiar face, and a sad one at that. I blearily rubbed my sleep filled eyes, “Dean?” I’m sure he could hear the confusion in my voice. 

“Sammy left,” He said dejectedly.

Without thinking I reached out for him and pulled him into my arms half expecting him to resist but instead he collapsed on to my shoulders. Releasing him, I nudged the door open a little more and pulled him farther inside. Quietly I led him into the kitchen and handed him a beer. 

“He left us, he left the life,” Dean mumbled.

“Yeah, umm he told me a while ago that he got into Stanford. I kinda figured he might,” I guiltily ran my hands through my hair. 

“He did? He sure as hell didn’t tell dad and me,” he stood up, running his hands over his face.

My legs, working on their own, carried me across the room until I was right in front of him, “Dean. You know he didn’t leave because he wanted to leave  _ you _ , right?” I said putting my hand on his arm. 

He rolled his eyes, “Yeah,” 

“Hey, I mean it,” My voice was soft but firm. “You’ve always looked out for your brother, he knows that.” I was met with sullen silence. 

After a few minutes of quietly sipping on our drinks he spoke up. “I mean I know this life ain’t easy but college, man!?”

“You know the boy’s always liked school,” I said jokingly, trying to lighten the mood. It did not work. “Alright. Are we getting drunk then?”

“Yep,” he said after downing the rest of his beer, “you got anything stronger?”

“Oh do you doubt me, Winchester?” I got up and opened the pantry to show the assortment of liquor bottles.

“Well then,” he raised his eyebrows as I dropped a bottle of whiskey in front of him, keeping the vodka for myself.

Once Dean had made it most of the way through his bottle he seemed more nostalgic than sad, “Do you remember back in high school…” he paused to take another drink, “when you thought Sammy needed to be taken care of?”

“Hey! In my defense he was very small then! And he did get picked on,”

“Ok, fair enough” he raised his hands in defense, “I’m glad you had his back,”

“Yeah well, someone had too since you kept getting in trouble,” It continued on like this for a while until I had deemed it time to cut Dean off and make him go to bed. “Alright come on, I’ll get you settled in my room,”

Just as I was leaving the room I heard a voice behind me, “do you think he’s gonna come back?”

“Honestly? I don’t know, but I know that just because he went off to school doesn’t mean he doesn’t love you,” I said turning back towards him and sitting on the bed.

“Psh. I know dads not the biggest joy in our lives but why can’t he just suck it up?” My heart broke when his voice cracked. Even in the dark I could tell he was tears eyed. 

“He and your dad have always had a tricky relationship,” I commented, scooting closer to him.

“Yeah,” he scoffed, “you should have seen it the night he left,” I could see on his face that it had gotten bad between them that night.

“I never liked your father,”

“He didn’t like you much either,” he admitted.

“Well, I’d imagine not!” It got quiet as we both remembered the first time I had met John Winchester.

_ Sam had invited me over to study for a history exam, even though I was a senior and he was a freshman we were in the same class. He was slightly embarrassed to tell me that he lived in a motel but that quickly faded once we got to studying. We were almost done when his brother came back.  _

_ “Heya Sammy,” _

_ “Dean! I thought you were supposed to be gone all day?”  _

_ “Eh, got bored,” he dismissed. Flopping down on one of the beds, opening up a magazine. “Dads gonna be pissed you brought her over,” _

_ “What is your problem with me Dean?” I spoke up, I wasn’t gonna let Sam get pushed around like that. _

_ “I don’t care either way, but dad doesn’t like us having people over,” As if on queue an older man opened the door. _

_ “Boys,” He gruffly acknowledged the boys, not noticing me at first, “who’s this?” He gestured to me, his voice making it clear that there was more involved in his question. _

_ “Oh, umm,” Sam stuttered. _

_ “I’m Y/N, I was helping Sam study but we were just finishing up,” I jumped in trying to help the poor boy out. _

_ “Well Y/N, it’s probably about time you were heading out. I have some business to discuss with my boys.” _

_ In class the next day Sam barely looked at me, and Dean-well Dean never paid me much attention anyway. After the bell rang I ran after Sam before Dean could drive off. _

_ “Sam! Wait up dude,” he ignored me until I was close enough to grab his elbow, “Hey, what’s wrong? It’s like you were somewhere else today,” _

_ “Oh, uh, hey Y/N,” he was clearly avoiding the question. Out of the corner of my eye I saw Dean walk up to the car, seemingly hiding his face.  _

_ “Come on Sammy, get in the car,” As he got in the car I caught a glimpse of a purple bruise on his jaw. _

_ “Um sorry, we have to get home before Dad” Sam explained shyly. As they drove away I connected the dots between Dean’s bruise and their fear of their father. Right then and there I decided I was going to protect Sam as much as I could, I doubted Dean would let me but I knew I was gonna try. _

  
  


“You should probably get some sleep,” Dean’s voice was hoarse, and much closer than I had realized. At some point we had ended up leaning on each other, slumped in the center of the bed. 

“Alright, but I’m not leaving you here to be sad and alone so don’t hog all the covers,” I sleepily shuffled under the blanket, Dean sliding in beside me. He fell asleep almost immediately, but me? I was laying there trying to wrap my brain around this version of Dean, the version thats cocky and tough I’m familiar with but this vulnerable and insecure Dean is a side I hadn’t seen before. Somewhere in the night we had ended up wrapped in each other's limbs, his head on my chest, his arms circling my waist. 

Dean was still asleep when I woke up; I laid there with my hand in his hair, realizing that this was as relaxed as I had been in a long while and I was in no rush to wake him up. We stayed like that until Dean started to stir,

“Morning sleepyhead,”

“Oh uh, mornin’,” he mumbled, rolling away seemingly embarrassed.

“How ya feeling after last night? You downed most of that whiskey,” I teased, poking his shoulder.

“Ha-shut up, I’m fine”

“Well, personally I am  _ severely  _ under-caffeinated so I’m gonna go make coffee,” I said definitively, pushing myself up heading to the kitchen. Dean got up and followed me, pointedly ignoring how we woke up. 

“You wanna coffee?” I asked, reaching up to the cabinet where my favorite mug was.

“Yes, please,” he said emphatically, running his hands over his face to wake himself up a little. 

“Ok, you gotta tell me more about what you and your brother do,” I slid a mug across the island to him, “I mean he told me a little bit about the life, and you’ve filled me in a little, but I’m curious,” 

“Nah, you don’t need to know how fucked up the world actually is,”

“Please. I already know the world is a flaming piece of garbage, you wouldn’t be bursting any bubbles with that realization,” My voice came out more cynical than I meant. 

“You really wanna know? About all the things that go bump in the night? All the monsters who are dying to eat your face?”

“Yeah. If I’m gonna have to live in the world with all that crap then I’d like to at least know what’s what,” I didn’t expect him to actually tell me, but he launched into stories about the creatures that he and Sammy have fought. We talked for hours, me asking questions, him telling stories. By the time he seemed to have run out of stories and he deemed I was sufficiently afraid it was early afternoon.

“Shit, is it already three? I should get on the road soon,”

“Do you have to? You can stay here another night, ya know,” I hoped he would stay.

“Are you sure? I don’t wanna over stay my welcome, I already showed up out of the blue-“

“Dean. You’re staying.” I interrupted, “you can show up any time, I like the company,” 

After convincing him to stay we ordered pizza and settled in for a chill night of movies and beer. 

After we stuffed ourselves with pizza and watched as many shitty comedies as we could handle, we were tipsy and sleepy and I made the executive decision that it was time for us (well, at least me) to crash for the night. After telling Dean he could watch whatever he wanted I headed into my room, put on comfy clothes and got curled up under the covers. A while after, when I was just starting to drift off I heard the door open,

“Hey, Y/N? You still awake?”

“Hmm? Yeah,” my vioce was thick with sleep.

“Can I- um can I sleep in here again?” He sounded so timid, not at all like the over confident persona he normally put on.

“Of course, come ‘ere,” I smiled, pulling the blankets down on the other side of the bed. He took his jeans off leaving him only in his boxers and climbed in next to me.

“You sure this is ok?” He asked again before fully relaxing.

“Dude, if I wasn’t chill with it I wouldn’t have said yes. Plus, you slept in here last night anyway,”

“I know, and we ended up the way we did this morning and I just- I wasn’t sure-“ I cut him off by pulling his arm over my side and shushing him. With him as the big spoon I think he had gotten it through his head that I wanted him there. 

“Hey dean?” He grunted in acknowledgment, “You show up here after almost four years, I just- I gotta ask, why here? Why did you come to my door?” He was silent for a long time, I thought he may have fallen asleep.

“Honestly?” I nodded, “I don’t know, you were one of the few people who knew Sammy like I did, and who knew about our lives,” he paused, “I think it just seemed the least complicated place to go.” He finished quietly.

“Fair enough, I’m glad you did though. I worry about you boys,” we fell back into a comfortable silence before he spoke again.

“Ok, my turn to ask something,” I twisted until I was facing him.

“Go for it,”

“Why is it just you living here? Doesn’t it get lonely?”

“Sometimes, but I like having the place to myself,”

“I always liked to think that after Sammy I left, you would have shacked up with some dude and lived the apple pie life,” 

“Oh please. You know that’s not my style,” I scoffed, “and as far as me and dudes there’s never been anyone of importance,”

“Really? No one?” He seemed surprised by this.

“What? Is it so hard to believe?” 

“But why?”

“You’ve met me, you know feeeelings aren’t my thing,”

“Ok but like what about hookup or something, you did go to college right? Isn’t that part of college life?”

“I don’t like doing new things with strangers, it is what it is. I’m not upset about it,” I shrugged.

“Just wouldn’t have pegged you as a virgin,”

“Oh I give off slutty vibes do I?” I teased him.

“No- I just- never mind,” I could practically see him mentally smacking himself in the forehead.

“Good night, Dean,” I rolled back over and he wrapped his arm back around my waist.

The next morning I woke up with Dean still pressed against my back, I don’t know if we moved at all in the night. I just knew that I slept like a rock. And that there was something poking me in the back. It took me a minute to figure out what it was but when it dawned on me I couldn’t help but giggle a little bit.

“Hey, ummm, Dean?” It came out higher than I meant it to.

“Hmm?” He sleepily responded, “oh shit, Y/N I’m sorry, I didn’t mean- it just-it does that sometimes,” He moved away from me covering his face with his hands.

“I didn’t say I was upset about it,” I slowly pulled his hand down until he could see me.

“What…. Y/N..? Huh?” You’d think he was the virgin not me.

“I said, I wasn’t upset. I just thought you should know that your dick-“

“Whoa! Ok, enough,” he cut me off. Turning his body to face me, our faces closer together than before, “are you serious?”

“Why wouldn’t I be?” My voice came out thin and whispery, but I leaned towards him anyway. I could almost hear my heartbeat in my ears, but the second that his lips touched mine that was the only thing I could focus on. After a second he pulled back with a questioning look in his eyes, I nodded and he kissed me again. Harder this time, his tongue finding its way into my mouth, my hand to his hair, his hands...everywhere. We stayed like that for a few minutes before he pulled away again, this time taking his whole body a few inches away from mine pulling a needy whine (that I will deny ever happened) out of me.

“Wait...wait, we can’t do this,” he said breathlessly.

“And why the hell not?” 

“You’ve never…your first shouldn’t be me,” 

“Why not. You’re not a stranger and there doesn’t need to be feelings. Checks all my boxes,”

“Oh wow, you sure know how to make a guy feel special,” I rolled my eyes and pulled him so his face was close to mine again.

“We don’t have to if you don’t want to, but I want this. You’re not taking advantage or anything like that, ok?” That was all he needed to hear before pushing himself so he was hovering over me, mouth back on mine, hands in my hair. Soon his mouth moved along my jaw and down my neck making sounds come out of my mouth that I didn’t think I could make. I could feel him smirking as he moved back up to my jaw. I could feel his hands start to migrate under my shirt, stopping just below my rib cage. I knew he was waiting for permission before going any farther so I pushed him onto his back before tearing my shirt off and leaning over him so I was on top. 

“No bra?” He questioned his hand automatically going to my boobs, flicking one of my nipples.

“Who sleeps in a bra?” I tried to say it jokingly but his mouth found my other nipple making it turn into a gasp. I tried to get back at him by grinding my hips down on the bulge that was now under me. He made a delicious gasp/moan sound that just made me never want to stop. I slowly shifted myself, kissing my way down his chest, giving attention to each nipple as I passed it, eventually making my way down to his happy trail and the edge of his boxers.

“Ahh…..sweetheart… you don’t-you don’t have to do that. Not... for your first time,” 

“Oh, but what if I want to?” The words came out sugary sweet, just the thought of what was about to happen was enough to dampen my underwear. I looked up at him for permission and he nodded, his eyes closing when I turned my attention back to the waistband of his boxers. He moaned loudly when I placed soft kisses on his fabric covered length before I pulled his shorts down and he kicked them the rest of the way off. Once he was fully exposed I took a second to admire what I saw; the toned muscle of his chest, the soft skin on his stomach, all the way down to his perfectly pink cock standing up out of a bush of dark curls.

“Like what you see?” He teased.

As an answer I leaned back down and licked a stripe from his balls all the way up to his leaking head. I earned a gasp and then a groan when I took the whole head into my mouth hollowing my cheeks and taking in as much of him as I could, one hand coming up to pump the part that I couldn’t fit in my mouth and the other reaching up and playing with his balls. 

“Holy….you shouldn’t be..how do you….” He gave up trying to make coherent sentences when I took his dick out of my mouth and sucked one of his balls. Once I had given them enough attention I moved back to his shaft, lavishing it in kisses and licks.

“Ok...I’m not gonna…. you gotta stop… if you want this to last…” he brought his hand to my face and pulled me back up so he could kiss me. His other hand came around my hip and flipped us so he was hovering above me with a shiteating grin on his face. It was his turn to tease me, he moved down so his face was right above my belly button. His fingers hooked into the waistband of my sleep shorts pulling them off. As soon as he had me naked he went back to kissing and licking everywhere he could, after some pleading from me he finally moved back between my legs where I needed him most. He licked a stripe between my folds, giving extra attention to my clit. I could feel the knot in my stomach tightening already, my breathing getting faster. He was still swirling his tongue in circles when one of his large fingers pushed into me making me moan and arch my back, pushing impossibly closer to his face. I could feel him smiling as he continued to work his finger in and out of me, eventually adding another curling them upward reaching that one spot that I could never quite reach myself. The knot in my stomach tightened even more, my hips bucking on their own.

“D.. I’m close..”

“Let go baby, I wanna taste it,” that’s all it took for me to cum on his face. Blissed out and breathing heavily I almost missed Dean looking smug wiping my juices off of his chin. 

“We don’t have to keep going…” he said and I think he really would have been totally fine stopping if I asked but I was nowhere near ready to be done.

“Condoms are in the nightstand,” was my bold way of saying I wanted to keep going. I could tell it caught him by surprise but before I could say anything else he had plopped himself on top of me to get to the drawer.

“Eager much?”I laughed as his full body weight was still splayed over me. He rolled his eyes and kissed me again rolling the condom on. I could feel his hard length resting against my stomach as we kissed, all tongues and teeth. We had gotten past the timid part and were both ready for more. He shifted and I could feel the tip hit my sensitive clit making me gasp, his cock slid between my folds and pushed into my entrance, he stopped making sure I was good before he slowly pushed the rest of the way in. Once he was fully seated inside me, his head fell down on my shoulder, his lips moving on my neck. I got impatient and moved my hips making him slip out a little bit, Dean took the hint and started to move. His pelvis hit my clit every thrust and he one of his hands came up and played with my nipple, I was overwhelmed by all the new sensations that I didn’t even realize I was making sounds that I had never made before. With each movement dean hit that spot inside that made my eyes roll back, before long I could feel the knot tightening again. Deans thrusts started to get shaky and uneven,

“I’m not gonna last…” he grunted, his face buried in my neck.

“Me… neither,” my hips bucked and with one more snap of his hips I came undone. That was all it took for him to spill himself into the condom. He collapsed next to me throwing the condom in the trash.

“Well….” I exhaled, breathing heavily.

“Yeahhh…” deans breathing matched my own.

“Soo, I’m not a virgin anymore,”

“No you are not,” He sounded real happy with himself. And honesty, and couldn’t blame him.

“Job well done I’d say,” I reached over to high five him. 

We laid there in exhausted silence for a while before either one of us had enough energy to do anything.

“Well, I am starving and there is cold pizza in the fridge,”I declared as I got out of bed and threw on some comfy clothes. I was halfway through my second piece of cold pizza when dean came trudging out of my room. With my mouth full of pizza I gestured to the open box.

“So…” Dean awkwardly rubbed the back of his head, “you’re really good with what just happened?”

“Why wouldn’t I be? Organs and pizza is a good way to start the day,”

“I don’t know, I mean it was your first time?”

“Oh D, are you worried I’m gonna fall in love with you?” I mocked.

“What no- I just- I was checking on you is all!”

“Ohhh little defensive much? Maybe I should worry about you falling in love with me,” I teased waving pizza in his face. 

When we had finished making fun of each other the topic turned serious.

“So, you gonna head back to your dad today?” I asked.

“Yeah, I should actually head out soon,” he said quietly. We chatted for a while longer before he decided it was time for him to go. He gathered his things and made his way to the door,

“Just one thing before you go,” I stopped him in the doorway, “give your brother a call, ok? He walked out on your father not on you,”

“Yeah, I will. Thanks sweetheart,” he hugged me and then he was gone. It had been four years since I met him in high school and I wondered if I would ever see the green eyed hunter again. But i sure hoped I would see him again.

  
  


**Author's Note:**

> feedback is much appreciated!!


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